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Fabrizio Miccoli curled in direct from the corner flag to earn Italy a morale-boosting victory in Portugal.
Giovanni Trapattoni fielded an experimental line-up that adopted Milan's 4-3-1-2 system with Andrea Pirlo, Gennaro Gattuso and Lazio's Stefano Fiore in midfield.
Francesco Totti acted as support for Christian Vieri and Carlo Nervo. The Bologna winger was drafted in a few hours before kick-off as first choice Marco Di Vaio pulled out with an infection.
These two teams last met in Genoa in Feb 2003 and Italy won 1-0 thanks to Bernardo Corradi's goal. Portugal have not beaten the Azzurri here in 27 years, since a 2-1 friendly result in Dec 1976.
It was also a special occasion, as the Azzurri unveiled the new team strip designed by Englishman Neil Barrett. Gianluigi Buffon was handed the captain's armband on his 44th international appearance.
Italy had the first real scoring opportunity after three minutes when Nervo ran on to Fiore's through ball and forced Ricardo Pereira to rush off his line and clear.
However, moments later it was Portugal who scored with the aid of a Milan star. Manuel Rui Costa's backheel completed the triangle with Nuno Valente and the defence left him unmarked to pierce Buffon's net at the near post.
This was the first goal that Portugal have scored against Italy since 1993 and Nuno Valente's first international strike.
Soon after Pauleta's long-range effort was deflected wide, then the lone striker fired wide after a defensive error from the reshuffled Azzurri back line.
The home side had a very confident start to the game and after that goal began to dominate possession. Andrea Pirlo's curling effort was between a cross and a shot.
Following an initial 15-minute spell of Portuguese pressure, Italy began to increase their influence and Nuno Valente dived in front of Totti to deflect his fierce drive just over the crossbar. On the resulting corner Christian Panucci and Giuseppe Pancaro were unable to make the most of some chaotic defending.
However, the Azzurri were left exposed to the counter-attack and Pauleta was ready to double Portugal's lead, but Panucci just managed to toe-poke the ball off his foot in a perfectly-timed intervention.
It became a more open game and Fiore hesitated too much to make the most of Gattuso's precise long pass, cutting back for Totti to drive it wide.
Trap's men were more dangerous and drew level just before the break. Totti took a free kick quickly and Christian Vieri rose to nod in, although there were Portuguese protests at an alleged push on Paulo Ferreira. It was Vieri's 21st international strike.
As expected, Trapattoni made several changes during the half-time break and introduced Fabrizio Miccoli, Massimo Ambrosini, Simone Perrotta and Giuseppe Favalli. Portugal also threw on Cristiano Ronaldo, Deco and Boa Morte.
There were some familiar faces all round and a scuffle broke out between Vieri and Fernando Couto as the Lazio defender was struck in the face by an outstretched hand.
The row continued several minutes later and both were booked for their off the ball battle. This incident rushed Trapattoni's decision to replace the Inter striker with Bernardo Corradi, while Massimo Oddo stepped in for Panucci, but Vieri walked straight past the bench and into the changing rooms.
Buffon tipped a deflected Luis Figo cross over the bar, then blocked a dangerous Deco free kick that bounced perilously in front of him.
Mauro German Camoranesi replaced Fiore in midfield as Italy returned to the old 4-2-3-1 system used during the latter period of qualifying.
The Argentine-born star ran into the box but fell under Boa Morte's mis-timed challenge, although the referee waved away penalty appeals.
Some wonderful approach play put Corradi in a great scoring position, but he was just offside.
Moments later Miccoli burst into the box after skipping past a challenge and drawing out the 'keeper, but a goalline clearance prevented Corradi turning into an empty net.
On the resulting corner Italy took the lead as Miccoli's swerving set-piece took everyone by surprise at the near post. Boa Morte's attempted clearance perhaps confused the goalkeeper in a bizarre goal.
The pitch was increasingly fast from the driving rain and Miccoli again rushed down the flank, but his cross was fingertipped just past the unmarked Simone Perrotta.
A clearly shaken Portugal fought back, but Buffon tipped a tight cross just far enough to miss the striker at the back post.
Boosted by his previous effort, Miccoli again attempted to curl the ball in directly from the corner flag, but this time a defender was able to clear off the line.
Buffon was again tested to palm out a fierce Beto drive from distance that bounced on the soaking wet surface. In stoppage time Nuno Gomes was ready to turn in before Matteo Ferrari's sliding tackle saved the result.
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